Fashion Dos And Don'ts: What You Should Learn From The World's Flashiest Dressers

Male celebrities have been dressing in bold and eccentric ways ever since Elvis first put on that rhinestone-encrusted white suit. This kind of outlandish approach to style has trickled into every facet of popular culture, from music to television to sports.

Male celebrities keep pushing the style envelope further and further, and while some of their unusual sartorial choices become fashion trends, others become the subject of much head-shaking and ridicule. What can you learn from the triumphs and pitfalls of these eccentrically dressed men? Here are some of pop culture’s most insanely dressed men, and what style tips you can take away from their zany closets.

Don CherryCredit: CBC

Canadian hockey commentator Don Cherry is best known for his flamboyant suits—elaborately patterned and brightly colored, often accompanied with matching ties. His style adds a much-needed element of visual panache to a sport that otherwise couldn’t compete with the fashion legacy of other sports (basketball jerseys are always cool but wearing a hockey jersey on a night other than game night makes you look like a dork). His style may seem too big to replicate, but what nuggets of sartorial wisdom can you take from Mr. Cherry’s bold and unconventional fashion choices?

What You Should Steal From Him: It is easy to get comfortable with traditional formalwear, but the repetition of black suit jacket/black tie, black suit jacket/black tie can get tiresome after a while. If you’re getting bored with your dull formalwear, change it up Don Cherry style — don’t be afraid to invest in a bright or patterned tie. Small accessories like cufflinks and pocket squares can also add flair to a more formal look without drawing too much attention. It’s good to keep a few of these colorful or outlandish pieces at the back of your wardrobe to protect against black tie monotony.

What You Shouldn't Steal From Him:First of all, there’s a time and a place for a funky tie. Wearing a flamboyant suit to a party is one thing, but if you show up to a meeting dressed like Willy Wonka you’re probably not going to get a promotion any time soon. Secondly, there’s a difference between adding some flare to your style and dressing like a used car salesman. Sometimes Don Cherry looks more like a clown at a children’s birthday party than someone who belongs on TV. Don’t go overboard with crazy ties and pocket squares or no one is going to take you seriously.

Dennis Rodman

Another sartorial standout in the sports world, Dennis Rodman often got more press for his unusual fashion choices than his performance on the court. Though no longer in the spotlight, his signature facial piercings and his vibrantly dyed hair have a permanent place is basketball history. He is maybe best remembered for his more controversial fashion choices, such as wearing makeup and dressing in drag from time to time. While Rodman may not be everyone’s cup of tea, every guy can learn a thing or two from his unusual and daring style.

What You Should Steal From Him: Whether or not you like the way he dresses, you have to admit that Dennis Rodman has confidence. If you’re going to make a bold and unconventional fashion choice, do it like Dennis Rodman — go big or go home. Don’t buy the ridiculous pants or get that crazy haircut if you’re not willing to stand behind it one hundred percent. Dennis Rodman’s swag is insane — even in his most garish outfits, he’s just looking at everybody like “what? I still make more money than you.” If you’re going to make a big statement with what you wear, you better have the balls to back it up.

What You Shouldn't Steal From Him:Dennis Rodman’s style can be a bit erratic. One day he’s wearing shades and baseball cap, the next day he’s got a foot-tall blond mohawk, then suddenly he’s in a wedding dress. Eventually, you have to stop playing dress-up and start dressing like a grown-ass man, which means developing a little consistency in your style. Also, not everyone can get away with two hoops in their nose and an eyebrow and lip piercing without looking like a pathetic high school burnout.

Andre 3000

Since the '90s, Outkast's Andre 3000 has been pushing the boundaries of what’s sartorially acceptable in hip-hop and his style has become one of the most original and iconic in the entire music industry. Some of his more outlandish outfit choices include white wigs, large faux-fur jackets, wide-legged plaid pants, and the slogan-covered black jumpsuits he designed and wore last year during the Outkast reunion tour. Most of us couldn’t measure up to Three Stacks, as they call him, but we can still take something away from his quirky fashion tastes.

What You Should Steal From Him: Andre 3000’s style success is all in the details. He doesn’t just throw on a bunch of zany clothes and stroll out onto the street. You can tell that dude’s put some thought into what he’s wearing, that the choice of hat, or how he does his hair, or how much he rolls up the cuff of his pant are all important elements of the overall outfit to him. If you want to look as smooth as Andre, you have to pay attention to the details. A stain on your shirt or an ill-fitting pair of pants is all it takes to make you look like a deadbeat slob. You don’t have to spend all day primping in front of the mirror, but for God’s sake at least check that your fly is zipped up before leaving the house.

What You Shouldn't Steal From Him:This one is harder because, full disclosure, I’m a big fan of the guy and don’t see much wrong with the way he dresses. What I will say is that Andre 3000 is a big fan of the fedora. He can pull it off because he’s Andre 300, and if Andre 3000 wants to wear a fedora, nobody can tell him otherwise. But for most people who aren’t Andre 3000, fedoras are hard to wear without looking like a big dweeb. Who do you think you are, Frank Sinatra? The '50s are over — take off the stupid hat and try again.

Jared Leto

Credit: Getty Images

Jared Leto is a hard one to miss, whether he’s on the Oscars' red carpet or singing lead in his band Thirty Seconds to Mars. In recent years, the actor and musician has traded in his pop-punk eyeliner for a scruffy beard and a long mane of hair. Even though he's dressing in more classic suits-and-ties these days, Jared Leto has kept the signature flair that made him a style icon since his television debut on My So-Called Life back in the '90s.

What You Should Steal From Him: Jared Leto is extremely true to himself in the way that he dresses. When Leto went on stage to accept the Oscar for best supporting actor for his performance in Dallas Buyers Club, his long locks went on stage with him. I bet he had a bunch of stylists hounding him to cut it off, but he kept his long hair even though it went against Hollywood convention. If you really like something, it’s your right to wear it, so who cares what a bunch of fashion snobs say? Not every style tip is going to apply to each person, so take a page from Jared Leto’s book and dress however the hell you feel like dressing.

What You Shouldn't Steal From Him:All that sappy self-help stuff I just said notwithstanding, you probably shouldn’t grow your hair out like Jared Leto. He looks like Jesus, and when his beard is fully grown out, he looks like homeless Jesus. There’s a fine line between being true to yourself and dressing like you just flat-out don’t care, and Jared Leto leans towards the latter. In my experience, you’re more likely to get more dates and better job offers if you look like you give a damn. Go to the barber regularly and remember to shave, or if you decide to grow out your hair, make sure it’s well-maintained.